Ethyl Acetate → 7-(4-Chlorophenyl)-5-methyl-6-vinylbenzo[d]thiazole

HRID 1468678Notes

Reaction equation

FC(F)(F)S(O[C:7]1[C:15]([CH3:16])=[CH:14][C:10]2[N:11]=[CH:12][S:13][C:9]=2[C:8]=1[C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)(=O)=O.[CH2:26](C([Sn])=C(CCCC)CCCC)[CH2:27]CC.[Li+].[Cl-].C(OCC)(=O)C>CN(C=O)C.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:23][C:20]1[CH:21]=[CH:22][C:17]([C:8]2[C:9]3[S:13][CH:12]=[N:11][C:10]=3[CH:14]=[C:15]([CH3:16])[C:7]=2[CH:26]=[CH2:27])=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 120 °C

Procedure

7-(4-chlorophenyl)-5-methylbenzo[d]thiazol-6-yl trifluoromethanesulfonate (5F) from above reaction was dissolved in DMF (3 ml). Tributylvinyltin (130 uL), PdCl2(PPh3)2 (27 mg, 0.039 mmol) and LiCl (49 mg, 1.17 mmol) were added. The reaction mixture was stirred at 120° C. in microwave for 30 min. The reaction mixture was diluted by ethyl acetate, washed with saturated NaHCO3 solution and extracted with ethyl acetate. The organic layer was dried over MgSO4, filtered, concentrated and purified by silica gel column (0-50% ethyl acetate/hexanes). LCMS-ESI+: calc'd for C16H20ClNS: 286.0 (M+H+). Found: 286.1 (M+H+).

Workup

washwashed with saturated NaHCO3 solution
extractionextracted with ethyl acetate
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
custompurified by silica gel column (0-50% ethyl acetate/hexanes)

Sources & evidence

ORD record: ord-938b1ac069b44827a5d61c45e54dba23
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09006229B2

Reaction notes

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